Growth Leadership – Executive IT Strategy Club

What you get with Growth Leadership

Everything in Essentials, plus the leadership program:

✔ Full access to the IT Strategy Portal and all Essentials content
✔ CEO-only online community and discussion hub – no MSPs or vendors
✔ Bi-weekly CEO Strategy Sessions (AMA format, 60–90 minutes) where we walk through selected member questions and live examples
✔ Monthly Vendor Intelligence Brief – short, practical analysis of vendor behaviour, pricing and contract tactics we’re seeing in the field
✔ Monthly CEO Strategic Decision Briefing – 2–3 page PDF on one key decision area (e.g. “Do we renew this MSP?”, “Is now the time for a cloud move?”, “What’s enough cyber for our size?”)
✔ Quarterly Peer Insights Benchmark – anonymous roll-up of spend, risk, cloud adoption and incident patterns across the club
✔ Early access to new executive toolkits – Growth members see new templates, checklists and scripts first
✔ Vendor quote assessment (1 per month) with a simple green/yellow/red summary and 3–5 line rationale
✔ Annual MSP contract sanity check for reasonableness and obvious gaps
✔ Annual IT maturity & risk snapshot – based on a structured executive questionnaire, with a clear score and prioritized fixes

How the bi-weekly CEO strategy sessions work

✔ Sessions run every two weeks for approximately 60–90 minutes
✔ CEOs submit questions in advance through the portal; submissions close Friday at 5:00 PM for the following week’s session
✔ Questions are curated and selected to cover a mix of cost, risk, vendor and roadmap topics that benefit the widest range of members
✔ We use real-world examples (sanitized) to keep the discussion grounded in business outcomes, not jargon
✔ Growth members can watch live or on replay, and apply the insights to their own situation

Why CEOs choose Growth Leadership:

✔ They want a structured leadership program around IT, not just ad-hoc advice
✔ They like seeing patterns across peers instead of making decisions in isolation
✔ They want to avoid expensive missteps on big decisions (cloud, MSP, security) while keeping 1:1 advisory optional
✔ They value an independent, vendor-neutral voice in the mix

Is Growth Leadership the right fit?

Good fit if:

✔You’re responsible for a growing team (10–50+ people) and IT is now board-visible.
✔You want a structured way to improve IT decisions over the next 12–24 months.
✔You anticipate cloud migrations, security upgrades or system changes in that window.
✔You like having a group of peers and vendor-neutral intel to sanity-check decisions with.

Consider Executive Advisory instead if:

You want a monthly 1:1 call dedicated solely to your environment and situation.
You have multiple vendors and high-impact projects already in motion.
Your board or lenders are actively asking IT-related questions and deadlines are firm.

Ask Whether Growth or Advisory Fits Better

Optional executive add-ons

These are one-time or per-instance engagements that can be added to any membership tier. We’ll always recommend the smallest option that genuinely fits your situation. Growth members often pair their membership with a Spend Baseline & Savings Map or Incident Tabletop in the first 6–12 months.

IT Spend Baseline & Savings Map

One-time review of your current IT spend (MSP, licenses, connectivity, backup, security) with a simple visual of where the money goes and 3–5 concrete savings opportunities.

✔Consolidate overlapping tools & services
✔Spot “auto-renew” traps and surprise costs
✔Map spend to business functions and risk

From $3,250 USD (up to ~50–75 staff). Larger environments priced by scope.

Board / Lender IT Briefing (Virtual)

A focused, plain-English briefing for your board or lender on current IT posture, key risks, and the short list of actions you are taking next.

✔Pre-call to understand your priorities & politics
✔Concise virtual briefing with Q&A
✔Short written summary you can reuse

From $3,750 USD per briefing. On-site board sessions available by request.

Incident / Ransomware Tabletop

Scenario-based exercise with your leadership team to walk through who does what, in what order, and with what information when something goes wrong.

✔Custom scenario tuned to your reality
✔Facilitated 90–120 minute live session
✔Gap list and next-step recommendations

From $2,750 USD per exercise (virtual). Hybrid and on-site options available.

On-Site Strategy Day

One day on-site with your CEO, leadership team and key IT stakeholders to align roadmap, spend, and risk with your actual business plans.

✔Pre-session call to shape the agenda
✔Full-day working session on-site
✔Written summary & 90-day action outline

From $5,250 USD plus travel (capped). Available to Advisory & Counsel members first.

Policy & Minimum Controls Pack

Lightweight tuning of core policies and minimum controls so you can demonstrate “reasonable steps” to staff, partners and insurers.

✔Acceptable use & remote work policy tuning
✔Backup / MFA / password baseline guidance
✔Light customization for your environment

From $1,950 USD one-time, depending on complexity and number of locations.

Note: All add-ons are scoped and confirmed in writing before any work begins. No long-term commitment is required beyond your selected membership tier.

Give yourself a structured CEO peer program for IT decisions.

Growth Leadership combines the structure of the portal with curated CEO strategy sessions and vendor-neutral intelligence – so you can make stronger IT decisions without yet committing to full 1:1 counsel.

Talk About Growth Leadership